ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 16.2, Problem 2P
Interpretation Introduction

Interpretation:

The structural formulae of the products of the given reactions that reflect the position of the deuterium atom in each of the product are to be determined.

Concept introduction:

The sodium borohydride (NaBH4) and lithium aluminum hydride (LiAlH4) act as a hydrogen donor compound.

The sodium borohydride (NaBH4) reduces the aldehydes and ketones to corresponding alcohols and the hydrogen atom that is bonded to carbonyl compound comes from borohydride.

The lithium aluminum hydride (LiAlH4) reduces almost all types of carbonyl compounds to their corresponding alcohols the hydrogen atom that is bonded to carbonyl compound comes from aluminum hydride

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a. What is the eluent used in the column chromatography here (a “silica plug filtration” is essentially a very short column)? b. The spectroscopy of compound 5b is described in the second half of this excerpt, including 1H-NMR and 13C-NMR (which you will learn about in CHEM 2412L), MS (which you will learn about later in CHEM 2411L) and IR. One of the IR signals is at 3530 cm-1. What functional group does this indicate might be present in compound 5b?
Steps and explanations. Also provide, if possible, ways to adress this kind of problems in general.
a. The first three lines of this procedure describe the reaction used to make compound 5b. In the fourth line, hexane and sodium bicarbonate are added. What organic lab technique is being used here?  b. What is the purpose of the Na2SO4?  c. What equipment would you use to “concentrate [a solution] under reduced pressure”?

Chapter 16 Solutions

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE

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